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Avoiding A CTO Meltdown: Part 2 - Warning Signs

There are some common warning signs when a CTO hits the wall and starts to struggle. Some of these are easy to see and others are more subtle, but the earlier everyone starts paying attention, the better.

This series of articles is based on conversations I had with Mark Uhrmacher, most recently CTO and founder of ideeli, the Internet fashion retailer that has pioneered the use of flash sales. He has worked as a technologist and CTO at all levels in organizations of many different sizes. In addition, he consults, under the umbrella of Simplifying Complexity, to help develop CTOs for many different companies and currently has a thriving consulting practice both as a coach for CTOs and as an adviser about technology strategy.

In Part 1 of this series we examined the job description of the CTO. When Uhrmacher presents that job description to CTOs he works with or those he helps informally, everyone quickly understands it. Often, CTOs confuse that understanding for actually having created an organization that can execute according to that job description.

In this article we will look at concrete evidence that a CTO may need some help or may need to improve the design and performance of the organization. The same disclaimer applies to these warning signs as we put forth about the definition of the CTO role: there are certainly many more than we list here, but in Uhrmacher’s experience, these are the greatest hits. Also, see Part 1 for the difference between the C-role and the VP Engineering-role of the CTO.

C-Role Warning Signs

The problems with the C-role usually center around the ability of the CTO to define plans, the role and responsibilities in a reasonable and clear manner, and to insist on adequate resources. When the CTO isn’t playing the C-role well the following sorts of problems crop up:

Lack of clear roadmap and detailed plans: If the CTO cannot present a roadmap about what is going to happen this quarter, next quarter, and beyond, it usually represents a large problem for the rest of the business. If a plan does exist, it should have logic, a rationale that explains the order in which things are taking place. Finally, a detailed plan that is constantly being reshaped and is never really authoritative is not much use to anyone. “For a CTO playing a strong game, you should be able to take the plan at the beginning of a quarter and compare it to the plan at the end of the quarter and be able to explain what happened, what didn’t happen, and why anything changed,” said Uhrmacher. “This is not easy, but it is essential.”

Never Saying No: In his biography, Steve Jobs was described as being quite proud of saying no. To Jobs, saying no, even to good or great ideas, was the ultimate sign of focus. But to say no and make it stick, you have to be able to explain why what you have said yes to is more important. In other words, you have to have a model of what you are going to do and the value that it is going to create. In addition, you need to show how many resources of all sorts (people, money, technology) are being employed. When CTOs always say yes and try to please their customer, little gets done well, and virtually nothing gets done on time. “A CTO must be able to articulate tradeoffs. If you give the business $1 to spend, they will spend 75 cents three times,” said Uhrmacher. “There is no quality of service without denial of service.”

Lack of confidence from above: It doesn’t take very long for a CTO to build or lose credibility after they have been put in charge. If the CTO comes through, often there is a sense of relief, a desire for more interaction. if the CTO suffers from some of the maladies just mentioned, the senior team loses enthusiasm and the CTO loses respect and credibility and can no longer function.

VP Engineering Role Warning Signs

The warning signs for the VP engineering role relate to the ability of the CTO to keep his or her promises.

Missing dates: Consistent inability to meet deadlines, especially those that were self-imposed, is usually clear evidence that project management practices are immature, although inability to plan and secure adequate resources can also contribute mightily. The causes of missed dates can include poor project planning, poor execution, and poor resource allocation. In larger organizations, inter-project coordination is often lacking, leading to mistakes in staffing the right level of capacity for each role. For example, the database experts may become 300% allocated because projects are planned in isolation. A variation on that theme is a high number hotspots such as the person who has to be on every project and/or a low “truck number” (the number of people who have to get hit by a truck to destabilize your team). Management teams love to think engineering time is a fungible resource. Estimating total person-hours or story points can be a useful high-level tool for rough project estimation but there is a natural specialization in every tech org so getting resource levels right becomes key to actually finishing projects on time.

Always saying no: Some CTOs realize that they are not able to create a credible resource model and instead of never saying no, they always say no. In such situations, CTOs effectively set expectations to zero. Then if anything gets done, hooray, it is a victory. Few CEOs or senior management teams accept this strategy for very long, but surprisingly, some do.

Poor customer satisfaction: When the C-suite and the lines of business feel that they are not getting what they need, the lack of ability to execute is often to blame. Again, this failure of confidence can have multiple contributing causes.

Low morale: In response to repeated failures and frustrations, CTOs often over commit resources, leading to frustration on the part of the people who are doing the work. There is only some many times that you can ask people to go the extra mile to make a poorly conceived deadline before they are overwhelmed with despair.

Retention and recruiting problems: A staff that is overworked without a clear mission, that is asked to do the impossible on a regular basis, typically suffers high turnover. Attracting top talent to join such as staff can also be difficult. It doesn’t matter if you are AppleApple Computer or the local pickle factory, people can feel when a team is having fun.

Lack of confidence from below: The final straw for a CTO can be a lack of faith from the troops, who may either complain to senior management, leave, or ask for a change.

The signs mentioned here usually aren’t all present at once. If they were, the company would be in full blown crisis. In addition, problems with proper performance of the C-role often show up in the VP of engineering-role.

While this list attempts to capture the most common signs of a meltdown, it is by no means exhaustive. We are eager to hear more from you about how to expand this analysis.

In the third and final part of this series, we will examine what a CTO can do to turn things around.

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It’s interesting that none of these warning signs include any actual, well, technology. While that may be close to correct — after all, people managing is a huge part of the job — I think there ought to be some warning signs specifically related to the technology in use in an organization. For example:

* Lack of dog-fooding. Organization doesn’t use its own tools. * Irrational dog-fooding. Organization is in a bubble using its own tools (Windows Phone at Microsoft) and ignoring vast switches in customer preference. * Brittle software. Things are always breaking. * “Three 9s” reliability, availability and performance. No full workday should ever be lost to customers or internal users. * Religious platform choices. * Vendor capture. No realistic alternatives to continuing with current vendor. * Non standard compliant tools. * Non participation in/awareness of open source.

All these should be warning signs to a CTO that he’s in trouble. They are certainly warning signs to the rest of his organization.